Madison Keys and Jessica Pegula are not only American tennis players in their early 30s, but they are also good friends.
Mixing work with play even more, the two are co-hosts, along with Jennifer Brady and Desirae Krawczyk, of The Players Box podcast, launched last year.
That’s why when the two met in the 2026 Australian Open Round of 16, Pegula’s agent wisely suggested they engage in a side bet.
The winner would have to fufill her side of the bet on the podcast.
Who Bet What?
Madison Keys wanted Jessica Pegula to wear a Kansas City Chiefs jersey with Travis Kelce and Taylor Swift markings on it. Pegula’s family owns the Buffalo Bills who often found the Chiefs as a roadblock to get to the Super Bowl so to call her unenthusiastic about doing this was an understatement.
Jessica Pegula wanted Madison Keys to try a Pegula family Thanksgiving staple: apple pie with cheddar cheese melted on top. Keys thought this sounded gross, and since she lost the match, she would find out if her hunch was correct.
What Madison Keys Thought About The Cheesy Apple Pie
Keys admitted that her cheese covered apple pie had been sitting around for a little while due to technical difficulties with the podcast.
Oh no…
Madison Keys at the apple pie with cheese on top of itpic.twitter.com/1ardxMBY96 https://t.co/a4DSFCezNC
— Barstool Tennis (@StoolTennis) February 3, 2026
She gagged before she took a bite on air and could not even finish chewing it before looking for someplace to spit it out.
Keys said it tasted worse than she suspected, as if someone mixed macaroni and cheese and apple pie together in a most unappetizing way.
She also said it looked like vomit on her plate.
Keys and Pegula will soon turn their sights to the Middle Eastern leg of the WTA tour while Krawczyk is currently playing doubles with Sofia Kenin at the Abu Dhabi Open.
Brady was set to play qualifying rounds for the Australian Open but opted to play Challenger events to get back in the groove after a 2 1/2 year layoff to recover from injuries.
